CN1030757A - 苯并噻唑衍生物 - Google Patents
苯并噻唑衍生物 Download PDFInfo
- Publication number
- CN1030757A CN1030757A CN88103660A CN88103660A CN1030757A CN 1030757 A CN1030757 A CN 1030757A CN 88103660 A CN88103660 A CN 88103660A CN 88103660 A CN88103660 A CN 88103660A CN 1030757 A CN1030757 A CN 1030757A
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- CN
- China
- Prior art keywords
- group
- lower alkyl
- pharmaceutically acceptable
- acceptable salt
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims abstract description 131
- 241001597008 Nomeidae Species 0.000 title description 6
- -1 benzothiazole compound Chemical class 0.000 claims abstract description 75
- 150000002617 leukotrienes Chemical class 0.000 claims abstract description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
- 208000006673 asthma Diseases 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000003814 drug Substances 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims description 5
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000043 antiallergic agent Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- AIRYDHVYJPMRTH-UHFFFAOYSA-N 4-[[(5,7-dibromo-4-hydroxy-1,3-benzothiazol-2-yl)amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NC2=C(O)C(Br)=CC(Br)=C2S1 AIRYDHVYJPMRTH-UHFFFAOYSA-N 0.000 claims description 2
- CZTHTGORNFWZRT-UHFFFAOYSA-N 4-[[(5,7-dibromo-6-hydroxy-1,3-benzothiazol-2-yl)amino]methyl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC1=NC2=CC(Br)=C(O)C(Br)=C2S1 CZTHTGORNFWZRT-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- GUAAQMHFGPSZEI-UHFFFAOYSA-N 4-[(6-hydroxy-4,5,7-trimethyl-1,3-benzothiazol-2-yl)amino]benzoic acid Chemical compound S1C=2C(C)=C(O)C(C)=C(C)C=2N=C1NC1=CC=C(C(O)=O)C=C1 GUAAQMHFGPSZEI-UHFFFAOYSA-N 0.000 claims 1
- MPDNGVXFXZXSBR-UHFFFAOYSA-N 5,7-di(propan-2-yl)-2-(pyridin-2-ylmethylamino)-1,3-benzothiazol-6-ol Chemical compound S1C=2C(C(C)C)=C(O)C(C(C)C)=CC=2N=C1NCC1=CC=CC=N1 MPDNGVXFXZXSBR-UHFFFAOYSA-N 0.000 claims 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 110
- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 3
- 201000010105 allergic rhinitis Diseases 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 206010020751 Hypersensitivity Diseases 0.000 abstract 1
- 208000026935 allergic disease Diseases 0.000 abstract 1
- 230000007815 allergy Effects 0.000 abstract 1
- 208000015606 cardiovascular system disease Diseases 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 55
- 239000002904 solvent Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000001035 drying Methods 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
- 238000003810 ethyl acetate extraction Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 9
- LXJOYRVJPWDJBZ-UHFFFAOYSA-N (2-acetamido-3-hydroxyphenyl)arsonic acid Chemical compound OC=1C(=C(C=CC1)[As](O)(O)=O)NC(C)=O LXJOYRVJPWDJBZ-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 239000000924 antiasthmatic agent Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000017858 demethylation Effects 0.000 description 5
- 238000010520 demethylation reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004663 dialkyl amino group Chemical group 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000003255 drug test Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- QVVAWONRFLJUBP-UHFFFAOYSA-N 1,3-benzothiazol-3-ium;chloride Chemical compound Cl.C1=CC=C2SC=NC2=C1 QVVAWONRFLJUBP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical class O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- XMLIIYMNDAGPGU-UHFFFAOYSA-N N=[Br] Chemical class N=[Br] XMLIIYMNDAGPGU-UHFFFAOYSA-N 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010070834 Sensitisation Diseases 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229960000265 cromoglicic acid Drugs 0.000 description 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- USLKCMBGQFYUFI-UHFFFAOYSA-N dichloromethane;tribromoborane Chemical compound ClCCl.BrB(Br)Br USLKCMBGQFYUFI-UHFFFAOYSA-N 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
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- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000000377 silicon dioxide Substances 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000012279 sodium borohydride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- LJDIOCJJKQCKEA-UHFFFAOYSA-N 2-amino-4-(dimethylamino)-5,7-di(propan-2-yl)-1,3-benzothiazol-6-ol Chemical compound CC(C)C1=C(O)C(C(C)C)=C2SC(N)=NC2=C1N(C)C LJDIOCJJKQCKEA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/84—Naphthothiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15098787 | 1987-06-17 | ||
| JP150987/87 | 1987-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1030757A true CN1030757A (zh) | 1989-02-01 |
Family
ID=15508808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN88103660A Pending CN1030757A (zh) | 1987-06-17 | 1988-06-17 | 苯并噻唑衍生物 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4929623A (fr) |
| EP (1) | EP0295656B1 (fr) |
| JP (1) | JP2793195B2 (fr) |
| KR (1) | KR910005709B1 (fr) |
| CN (1) | CN1030757A (fr) |
| AT (1) | ATE82276T1 (fr) |
| AU (1) | AU610186B2 (fr) |
| CA (1) | CA1322369C (fr) |
| DD (1) | DD282686A5 (fr) |
| DE (1) | DE3875809T2 (fr) |
| DK (1) | DK328888A (fr) |
| ES (1) | ES2045017T3 (fr) |
| FI (1) | FI91859C (fr) |
| GR (1) | GR3006207T3 (fr) |
| HU (1) | HU205347B (fr) |
| NO (1) | NO170929C (fr) |
| NZ (1) | NZ224946A (fr) |
| PH (1) | PH26553A (fr) |
| PT (1) | PT87747B (fr) |
| SU (1) | SU1731051A3 (fr) |
| ZA (1) | ZA884277B (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100546580C (zh) * | 2001-11-19 | 2009-10-07 | 弗·哈夫曼-拉罗切有限公司 | 烟碱或异烟碱苯并噻唑衍生物 |
| CN102872012A (zh) * | 2011-11-03 | 2013-01-16 | 成都医学院 | 一种抑制蛋白激酶的化合物及其用途 |
| CN102056933B (zh) * | 2008-04-11 | 2014-09-17 | 詹森药业有限公司 | 作为白三烯a4水解酶调节剂的噻唑并吡啶-2-基氧基-苯基和噻唑并吡嗪-2-基氧基-苯基胺类 |
| CN113959912A (zh) * | 2020-07-20 | 2022-01-21 | 深圳迈瑞生物医疗电子股份有限公司 | 抗血小板聚集干扰的白细胞检测方法、试剂及其应用 |
| CN113959911A (zh) * | 2020-07-20 | 2022-01-21 | 深圳迈瑞生物医疗电子股份有限公司 | 抗血小板聚集干扰的检测方法、试剂及其应用 |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE68903484T2 (de) * | 1988-12-15 | 1993-03-18 | Rhone Poulenc Sante | 2-imino-6-polyfluoralkoxy-benzothiazol-derivate, verfahren zu deren herstellung und arzneimittel, die sie enthalten. |
| IL97249A (en) * | 1990-02-23 | 1995-01-24 | Takeda Chemical Industries Ltd | Compounds of 7,6,5,4-tetrahydrothiazole] B-5,4 [pyridine and compounds of 5,6-dihydro-H4-pyrrolo] D-3,2 [thiazole, their manufacture, and pharmaceutical compositions including or |
| IE920921A1 (en) * | 1991-04-04 | 1992-10-07 | Eisai Co Ltd | Benzothiazole derivative |
| US5296486A (en) * | 1991-09-24 | 1994-03-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Leukotriene biosynthesis inhibitors |
| US5350760A (en) * | 1993-08-04 | 1994-09-27 | Merck Frosst Canada, Inc. | Aza-5,5-fused hetrocyclic acids as leukotriene antagonists |
| WO1997048694A1 (fr) * | 1996-06-20 | 1997-12-24 | Board Of Regents, The University Of Texas System | Composes et procedes d'obtention de preparations pharmacologiquement actives et leurs utilisations |
| ATE432078T1 (de) | 1997-11-13 | 2009-06-15 | Mowycal Lending Llc | Kleine peptide und methoden zur behandlung von asthma und entzündungen |
| GB9815696D0 (en) * | 1998-07-20 | 1998-09-16 | Pfizer Ltd | Heterocyclics |
| US6686357B1 (en) | 1999-07-15 | 2004-02-03 | Pfizer, Inc. | FKBP inhibitors |
| EP1150565A1 (fr) * | 1999-02-08 | 2001-11-07 | LION bioscience AG | Derives de thiazole et leurs banques combinatoires |
| EP1178977B1 (fr) * | 1999-05-12 | 2005-06-01 | Neurosearch A/S | Agents de modulation de canaux ioniques |
| TWI284639B (en) | 2000-01-24 | 2007-08-01 | Shionogi & Co | A compound having thrombopoietin receptor agonistic effect |
| JP2003532728A (ja) * | 2000-05-05 | 2003-11-05 | コー セラピューティックス， インコーポレイテッド | ヘテロ二環式スルホンアミドおよび血小板ａｄｐレセプターインヒビターとしてのそれらの使用 |
| US6750238B1 (en) * | 2000-05-12 | 2004-06-15 | The University Of Toledo | Aralkyl ester soft drugs |
| US7049326B2 (en) * | 2000-05-12 | 2006-05-23 | The University Of Toledo | Method and compositions for temporarily incapacitating subjects |
| US6756047B2 (en) * | 2000-05-12 | 2004-06-29 | The University Of Toledo | Method and compositions for treating persistent pulmonary hypertension using aralkyl ester soft drugs |
| AU2001281817B2 (en) | 2000-06-21 | 2005-11-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
| US6624163B2 (en) * | 2001-11-29 | 2003-09-23 | Hoffman-La Roche Inc. | Benzothiazole derivatives |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| KR100710453B1 (ko) * | 2003-05-13 | 2007-04-24 | 에프. 호프만-라 로슈 아게 | 아데노신 수용체 리간드로서의 2-이미다조-벤조싸이아졸 |
| PT1636223E (pt) * | 2003-05-19 | 2008-05-06 | F Hoffmann-La Roche Ag | Derivados de benzotiazole como ligandos de receptores da adenosina |
| MXPA05012369A (es) * | 2003-05-21 | 2006-02-02 | Hoffmann La Roche | Derivados de benzotiazol y uso de los mismos en el tratamiento de enfermedades relacionadas con el receptor a2a de adenosina. |
| RU2348629C2 (ru) * | 2003-05-30 | 2009-03-10 | Ф.Хоффманн-Ля Рош Аг | Производные бензотиазола и их применение при лечении заболеваний, связанных с аденозиновыми a2a-рецепторами |
| US20050118291A1 (en) * | 2003-09-10 | 2005-06-02 | Mian-Ying Wang | Formulations and methods for treating breast cancer with Morinda citrifolia and methylsulfonymethane |
| KR100776961B1 (ko) | 2003-08-12 | 2007-11-28 | 시오노기세이야쿠가부시키가이샤 | 트롬보포이에틴 수용체 아고니스트 작용을 가지는 화합물 |
| RS50574B (sr) | 2004-05-24 | 2010-05-07 | F. Hoffmann-La Roche Ag. | (4-metoksi-7-morfolin-4-il-benzotiazol-2-il)-amid 4-hidroksi-4-metil-piperidin-1-karboksilne kiseline |
| BRPI0514099A (pt) * | 2004-08-05 | 2008-05-27 | Hoffmann La Roche | composições farmacêuticas, compostos, processo para a sua manufatura, método para o tratamento terapêutico e/ou profilático de enfermidades e utilização dos compostos |
| ES2309814T3 (es) | 2004-11-05 | 2008-12-16 | F. Hoffmann-La Roche Ag | Proceso para la obtencion de derivados del acido isonicotinico. |
| WO2006099972A1 (fr) | 2005-03-23 | 2006-09-28 | F. Hoffmann-La Roche Ag | Derives d'acetylenyl-pyrazolo-pyrimidine comme antagonistes mglur2 |
| JP5048675B2 (ja) | 2005-09-27 | 2012-10-17 | エフ．ホフマン−ラ ロシュ アーゲー | ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類 |
| CN101410385B (zh) | 2006-03-28 | 2011-08-24 | 高点制药有限责任公司 | 具有组胺h3受体活性的苯并噻唑类 |
| UY32138A (es) | 2008-09-25 | 2010-04-30 | Boehringer Ingelheim Int | Amidas sustituidas del ácido 2-(2,6-dicloro-fenilamino)-6-fluoro-1-metil-1h-bencimidazol-5-carboxílico y sus sales farmacéuticamente aceptables |
| UY32470A (es) | 2009-03-05 | 2010-10-29 | Boehringer Ingelheim Int | Derivados de 2-{2-cloro-5-[(sustituido) metil]fenilamino} -1-metil]fenilamino}-1-metilbencimidazol-5-carboxamidas-n-(sustituidas) y sus sales fisiológicamente aceptables, composiciones conteniéndolos y aplicaciones |
| EP2408769A1 (fr) * | 2009-03-17 | 2012-01-25 | Glaxo Group Limited | Dérivés de pyrimidine utilisés comme inhibiteurs de ltk |
| US8759537B2 (en) | 2010-08-20 | 2014-06-24 | Boehringer Ingelheim International Gmbh | 3H-imidazo [4, 5-C] pyridine-6-carboxamides as anti-inflammatory agents |
| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| UY33779A (es) | 2010-12-10 | 2012-07-31 | Boehringer Ingelheim Int | ?2-(fenilamino)-1H-bencimidazol-5-carboxamidas novedosas? |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2617198A (en) * | 1945-06-13 | 1952-11-11 | Better Packages Inc | Pull-out measuring tape dispenser |
| DE927507C (de) * | 1953-02-24 | 1955-05-09 | Bayer Ag | Verfahren zur Herstellung von Derivaten des 6-Oxy-2-aminobenzthiazols |
| GB808191A (en) * | 1956-07-13 | 1959-01-28 | Robert Ronald Davies | New dyestuff intermediates |
| US4006242A (en) * | 1973-07-18 | 1977-02-01 | Schering Corporation | Certain benzothiazoles used in the treatment of helminthiasis |
| AR204835A1 (es) * | 1973-07-18 | 1976-03-05 | Scherico Ltd | Procedimiento para preparar benzotiazol-2-carbamatos de etilo |
| DK148476C (da) * | 1975-04-25 | 1985-12-16 | Scherico Ltd | Analogifremgangsmaade til fremstilling af methyl-6-n-propoxybenzothiazol-2-carbamat |
| JPS5221054A (en) * | 1975-08-11 | 1977-02-17 | Teijin Ltd | Polyamide composition |
| DE2656468A1 (de) * | 1976-12-14 | 1978-06-15 | Boehringer Mannheim Gmbh | N-(benzthiazol-2-yl)-oxamidsaeure- derivate und verfahren zu ihrer herstellung |
| DE2963316D1 (en) * | 1978-01-18 | 1982-09-02 | Hoechst Ag | Process for the preparation of 2-amino-arylenothiazole compounds and their ring n-substituted derivatives |
| JPS5740492A (en) * | 1980-08-22 | 1982-03-06 | Yamanouchi Pharmaceut Co Ltd | Novel 2-phenylimidazo 2,1-b benzothiazole derivative |
| US4581457A (en) * | 1984-09-21 | 1986-04-08 | American Home Products Corporation | Heterocyclic sulfonamides |
-
1988
- 1988-06-07 FI FI882692A patent/FI91859C/fi not_active IP Right Cessation
- 1988-06-08 NZ NZ224946A patent/NZ224946A/xx unknown
- 1988-06-15 ZA ZA884277A patent/ZA884277B/xx unknown
- 1988-06-15 DE DE8888109552T patent/DE3875809T2/de not_active Expired - Fee Related
- 1988-06-15 ES ES88109552T patent/ES2045017T3/es not_active Expired - Lifetime
- 1988-06-15 JP JP63147141A patent/JP2793195B2/ja not_active Expired - Lifetime
- 1988-06-15 EP EP88109552A patent/EP0295656B1/fr not_active Expired - Lifetime
- 1988-06-15 CA CA000569598A patent/CA1322369C/fr not_active Expired - Fee Related
- 1988-06-15 NO NO882627A patent/NO170929C/no unknown
- 1988-06-15 AT AT88109552T patent/ATE82276T1/de active
- 1988-06-16 SU SU884356028A patent/SU1731051A3/ru active
- 1988-06-16 HU HU883098A patent/HU205347B/hu not_active IP Right Cessation
- 1988-06-16 DD DD88316839A patent/DD282686A5/de not_active IP Right Cessation
- 1988-06-16 DK DK328888A patent/DK328888A/da not_active Application Discontinuation
- 1988-06-16 AU AU17699/88A patent/AU610186B2/en not_active Ceased
- 1988-06-16 US US07/207,329 patent/US4929623A/en not_active Expired - Fee Related
- 1988-06-16 PT PT87747A patent/PT87747B/pt not_active IP Right Cessation
- 1988-06-17 CN CN88103660A patent/CN1030757A/zh active Pending
- 1988-06-17 KR KR1019880007320A patent/KR910005709B1/ko not_active Expired
- 1988-08-08 PH PH37022A patent/PH26553A/en unknown
-
1992
- 1992-11-12 GR GR920401328T patent/GR3006207T3/el unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100546580C (zh) * | 2001-11-19 | 2009-10-07 | 弗·哈夫曼-拉罗切有限公司 | 烟碱或异烟碱苯并噻唑衍生物 |
| CN102056933B (zh) * | 2008-04-11 | 2014-09-17 | 詹森药业有限公司 | 作为白三烯a4水解酶调节剂的噻唑并吡啶-2-基氧基-苯基和噻唑并吡嗪-2-基氧基-苯基胺类 |
| CN102872012A (zh) * | 2011-11-03 | 2013-01-16 | 成都医学院 | 一种抑制蛋白激酶的化合物及其用途 |
| CN102872012B (zh) * | 2011-11-03 | 2015-03-25 | 成都医学院 | 一种抑制蛋白激酶化合物的用途 |
| CN113959912A (zh) * | 2020-07-20 | 2022-01-21 | 深圳迈瑞生物医疗电子股份有限公司 | 抗血小板聚集干扰的白细胞检测方法、试剂及其应用 |
| CN113959911A (zh) * | 2020-07-20 | 2022-01-21 | 深圳迈瑞生物医疗电子股份有限公司 | 抗血小板聚集干扰的检测方法、试剂及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2045017T3 (es) | 1994-01-16 |
| NO882627L (no) | 1988-12-19 |
| NO170929B (no) | 1992-09-21 |
| PH26553A (en) | 1992-08-19 |
| HUT47554A (en) | 1989-03-28 |
| ZA884277B (en) | 1989-03-29 |
| US4929623A (en) | 1990-05-29 |
| AU1769988A (en) | 1988-12-22 |
| PT87747B (pt) | 1992-10-30 |
| FI882692L (fi) | 1988-12-18 |
| FI91859C (fi) | 1994-08-25 |
| AU610186B2 (en) | 1991-05-16 |
| JPS6479162A (en) | 1989-03-24 |
| KR910005709B1 (ko) | 1991-08-02 |
| DK328888D0 (da) | 1988-06-16 |
| EP0295656B1 (fr) | 1992-11-11 |
| HU205347B (en) | 1992-04-28 |
| PT87747A (pt) | 1988-07-01 |
| NO882627D0 (no) | 1988-06-15 |
| JP2793195B2 (ja) | 1998-09-03 |
| CA1322369C (fr) | 1993-09-21 |
| FI882692A0 (fi) | 1988-06-07 |
| ATE82276T1 (de) | 1992-11-15 |
| EP0295656A1 (fr) | 1988-12-21 |
| DK328888A (da) | 1988-12-18 |
| FI91859B (fi) | 1994-05-13 |
| KR890000451A (ko) | 1989-03-14 |
| GR3006207T3 (fr) | 1993-06-21 |
| NO170929C (no) | 1993-01-06 |
| DE3875809D1 (de) | 1992-12-17 |
| SU1731051A3 (ru) | 1992-04-30 |
| DD282686A5 (de) | 1990-09-19 |
| DE3875809T2 (de) | 1993-04-15 |
| NZ224946A (en) | 1990-07-26 |
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